Acetic Anhydride → HCID 178473826, compound

HRID 389535Notes

Reaction equation

HRID 389535 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH2:15][C:16]1[N:17]=[CH:18][C:19]([C:35]2[CH:36]=[N:37][N:38]([CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[CH:39]=2)=[C:20]2[CH:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][N:30]=[C:31]([OH:34])[CH:32]=4)[S:27][CH:26]=3)[O:22][C:21]=12.C1C[O:49][CH2:48][CH2:47]1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH2:15][C:16]1[N:17]=[CH:18][C:19]([C:35]2[CH:36]=[N:37][N:38]([CH:40]3[CH2:45][CH2:44][N:43]([C:48](=[O:49])[CH3:47])[CH2:42][CH2:41]3)[CH:39]=2)=[C:20]2[CH:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][N:30]=[C:31]([OH:34])[CH:32]=4)[S:27][CH:26]=3)[O:22][C:21]=12

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178508360HCID 178508360, compound

Product 1

HCID 178473826HCID 178473826, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-{7-amino-4-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-2-yl}thieno[2,3-c]pyridin-5-ol bis(trifluoroacetate) (40 mg, 0.061 mmol), THF (3 mL), and DMF (1.5 mL) was added triethylamine (72 μl, 0.52 mmol) followed by acetic anhydride (5.9 μl, 0.61 mmol). After stirring at RT for 1 h, the reaction mixture was concentrated in vacuo, and was then purified by MDP to afford 2.0 mg (5%) of the title compound as a yellow paste. 1H NMR (400 MHz, DMSO-d6): δ 13.72 (br s, 1 H), 8.86 (s, 1 H), 8.74 (s, 1 H), 8.56 (br s, 2 H), 8.48 (d, J=0.8 Hz, 1 H), 8.12 (d, J=0.8 Hz, 1 H), 7.96 (s, 1 H), 7.88 (s, 1 H), 7.67 (s, 1 H), 4.48-4.58 (m, 2 H), 3.94-4.01 (m, 1 H), 3.22-3.31 (m, 1 H), 2.73-2.82 (m, 1 H), 2.07-2.18 (m, 2 H), 2.07 (s, 3 H), 1.79-2.02 (m, 2 H); MS (ESI): 475.14 [M+H]+; HPLC tR=0.96 min (TOF: polar—3 min).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customwas then purified by MDP

Sources & evidence

ORD record
ord-26f74e34e261415abcf31c3d11884182
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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